Dimethylformamide → HCID 18182268, compound

HRID 1359325Notes

Reaction equation

CN(C)C=O.FC(F)(F)S(O[C:12]1[C:13]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:14][C:15]([CH3:18])=[CH:16][CH:17]=1)(=O)=O.[C:29]([C:31]1([OH:39])[CH:36]2[CH2:37][CH2:38][N:33]([CH2:34][CH2:35]2)[CH2:32]1)#[CH:30].C(N(CC)CC)C>C(Cl)(Cl)Cl.CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:21]1([CH2:20][CH2:19][C:13]2[C:12]([C:30]#[C:29][C:31]3([OH:39])[CH:36]4[CH2:37][CH2:38][N:33]([CH2:34][CH2:35]4)[CH2:32]3)=[CH:17][CH:16]=[C:15]([CH3:18])[N:14]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 50 °C

Procedure

10 ml of N,N-dimethylformamide was added to a mixture of 1.2 g of 6-methyl-2-(2-phenylethyl)pyridyl trifluoromethane sulfonate, 522 mg of 3-ethynyl-3-quinuclidinol, 400 mg of tetrakis(triphenylphosphine)palladium(0), 217 mg of cuprous iodide and 1.7 ml of triethylamine, followed by heating under stirring at 50° C. in an oil bath for one hour in a nitrogen atmosphere. After cooling as it was, the reaction solution was sprinkled over silica gel and subjected to silica gel column chromatography using chloroform/methanol/aqueous 36% ammonia (46:5:0.5) as an eluent for separation and purification, to give 490 mg of the target compound.

Workup

temperatureby heating
temperatureAfter cooling as it
customfor separation and purification

Sources & evidence

ORD record: ord-da37f03d93bc474fa56b5ae646e312c0
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599917B1

Reaction notes

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